53 Highland Drive, Monroe, CT 06468
OFF MARKET

$403,300

Trulia Estimate
  • 2 Beds
  • 1.5 Baths
  • 1,011 sqft

53 Highland Drive, Monroe, CT 06468

East Village
Est. Refi. Payment $2,800/mo*
Refinance Your Home
Currently Off Market - Sold Jul 7, 2025 for $374,000

Home Value

Trulia Estimate
$403K
Since last month
Decreased$400 (-0.1%)
Since last year
Increased$23K (+5.9%)
Since last sale
Increased$29K (+7.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +83% in the last 10 years
MonthEstimated value
2026
September 2026$403K
August 2026$403K
July 2026$398K
June 2026$397K
May 2026$393K
April 2026$386K
March 2026$386K
February 2026$386K
January 2026$379K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Behrens Terrace #3, Monroe, CT
0.08
Condo
$360,000
02/24/26
2
2.5
1,011
140 Highland Drive #140, Monroe, CT
0.16
Condo
$329,900
01/06/26
1
1.5
1,011
11 Behrens Terrace #11, Monroe, CT
0.10
Condo
$399,000
08/14/26
1
2.5
1,187
154 Highland Drive #154, Monroe, CT
0.14
Condo
$362,000
09/26/25
1
1.5
2,011
35 October Lane #35, Beacon Falls, CT
2.45
Condo
$420,000
05/27/26
2
3
2,204
21 Rockview Circle #21, Monroe, CT
3.06
Condo
$330,000
06/16/26
1
1.5
1,159

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
49 Highland Drive #49, Monroe, CT 06468
0.02
$368,800
1
2.5
1,515
Off Market
51 Highland Drive #51, Monroe, CT 06468
0.02
$394,100
2
1.5
1,211
Off Market
43 Highland Drive #43, Monroe, CT 06468
0.04
$364,600
1
1.5
1,355
Off Market
53 Highland Drive #53, Monroe, CT 06468
0.00
$403,500
2
1.5
1,011
Off Market
55 Highland Drive #55, Monroe, CT 06468
0.00
$402,000
2
1.5
1,811
Off Market
57 Highland Drive #57, Monroe, CT 06468
0.01
$357,700
1
1.5
1,211
Off Market
37 Highland Drive #37, Monroe, CT 06468
0.06
$396,800
1
2.5
1,587
Off Market
28 Highland Drive #28, Monroe, CT 06468
0.06
$299,900
1
1
1,054
For Sale
31 Highland Drive, Monroe, CT 06468
0.07
$375,800
1
1.5
1,011
Off Market
29 Highland Drive #29, Monroe, CT 06468
0.07
-
1
2
1,011
Off Market
76 Highland Drive #76, Monroe, CT 06468
0.06
$420,300
1
2.5
1,631
Off Market

Local Information

  • Map ViewExplore the area around 53 Highland Drive.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 1995
1,011 sqft
$399/sqft
1 Car Garage
HOA $489/mo

About this House

Welcome to High Meadows! Monroe's 55+ Community is located on the Eastern edge of Connecticut's Fairfield County! Miles away from the Housatonic River's historic Stevenson Dam. Short drive to the NY border 23 miles+/- of Brewster on CT-I-84 and only 46 miles +/- I-95. This is an END-UNIT 1 Bedroom with 1.5 bathroom condo that hasn’t hit the market in over 20 years! Additional finished upper and lower levels with mechanical room for plenty of storage/workshop space. Washer and dryer on the main floor. Attached 1 car garage with additional parking. Clubhouse. Close to restaurants, entertainment, family farms/wine vineyards, ice cream shops, retail/food shopping, health care facilities/gyms and so much more! Come live in Monroe - a small town with New England charm!
53 Highland Drive, Monroe, CT 06468 is a 2 bedroom, 2 bathroom, 1,011 sqft condo in East Village, built in 1995. It last sold for $374,000 on Jul 7, 2025 (10% above the $339,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $403,300, with a rent estimate of $2,782/month.
Last check for updates: about 15 hours ago
Listed by Stephen Thrower, (203) 543-3438
Realty ONE Group Connect, (203) 590-1111
Bought with: Marissa Papa, (203) 331-7043, Preston Gray Real Estate, (475) 269-5100
Source: Smart MLS, MLS#170591678

Home Details for 53 Highland Drive

Interior Features

Interior Details
Basement: Partially Finished,Heated,Cooled,Storage SpaceNumber of Rooms: 4Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Loft, Rec Play Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1011 Square Feet
Appliances & Utilities
Appliances: Electric Cooktop, Electric Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Electric Water HeaterDishwasherDryerLaundry: Mud RoomRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,ElectricHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Common Walls: End Unit
Levels, Entrance, & Accessibility
Stories: 3Accessibility: Bath Grab Bars, Raised Toilet

Exterior Features

Exterior Home Features
Patio / Porch: Patio, Porch, EnclosedExterior: Rain Gutters, SidewalkNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageParking Spaces: 1Parking: Attached,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Shared Septic
Finished Area
Finished Area (above surface): 1011 Square Feet

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: ResidentialProperty Subtype: Condominium, ApartmentStructure Type: ApartmentArchitecture: Ranch,Apartment
Building
Building Name: High MeadowsConstruction Materials: Shingle Siding, Wood SidingNot a New ConstructionAttached To Another StructureDoes Not Include Home Warranty
Property Information
Not Included in Sale: Refer to Inclusion/ExParcel Number: 179229

Price & Status

Price
List Price: $339,000
Status Change & Dates
Off Market Date: Wed Aug 23 2023Possession Timing: Withheld

Active Status

MLS Status: Closed

Location

Direction & Address
City: MonroeCommunity: East Village
School Information
Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Masuk

Building

Building Area
Building Area: 1011 Square Feet

Community

Community Features: Adult Community 55, Golf, Lake, Library, Medical Facilities, Park, Public Rec Facilities, Shopping/MallIs a Senior Community

HOA

HOA Fee Includes: Maintenance Grounds, Trash, Snow RemovalHas an HOAHOA Fee: $489/Monthly

Miscellaneous

BasementMls Number: 170591678Attic: Walk-up, Finished, StorageAbove Grade Unfinished Area: 1011

Additional Information

HOA Amenities: Clubhouse,Management

Price and Tax history

DateEventPrice
Jul 7, 2025
Source: N/A
Sold
$374,000
Oct 20, 2023
Source: Smart MLS #170591678
Sold
$355,000
Aug 16, 2023
Source: Smart MLS #170591678
Listed For Sale
$339,000
May 10, 1995
Source: N/A
Sold
$139,900

Market trends in Monroe

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$645K
$27.48KMoM
Sale-to-List Price
100.2%
0.5%MoM
Price per sq ft
$279
$7MoM
Available listings
64
16MoM

Around this home

Neighborhood Overview

East Village
See Local Highlights
Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

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Frequently asked questions about 53 Highland Drive

  • What is 53 Highland Drive estimated to be worth?
    Trulia's estimated value for 53 Highland Drive in Monroe, CT is $403,300.
  • What is the price history for 53 Highland Drive?
    53 Highland Drive in Monroe, CT last sold for $374,000 in July 2025.
  • Is Monroe a buyer's or seller's market?
    Monroe is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Monroe?
    The median sale price in Monroe is $645K. That is down $27.48K from the prior month.
  • Does 53 Highland Drive have air conditioning?
    Yes, 53 Highland Drive in Monroe, CT has air conditioning.
  • Does 53 Highland Drive have laundry facilities?
    Yes, 53 Highland Drive in Monroe, CT has in-unit laundry.

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